Identification Of Pheromone Research Articles

Studies on the identification and syntheses of insect pheromones: XX. Synthesis of (7R, 8S)-(+)-sex pheromone of gypsy moth through the kinetic resolution of (±) allylic alcohol by Sharpless asymmetric epoxidation

The chiral epoxy alcohol (1, 2R)-epoxy-3S-tridecanol (3) was synthesized in 92％ e. e. according to kinetic resolution of (±) 1-tridecen-3-ol (2) by Sharpless asymmetric epoxidation. 3 was then transformed to (7R, 8S)-la, the sex pheromone of gypsy moth, in overall yield of 60％ in 5 steps.

Identification of pheromones from the male swift moth [formula omitted] l.

Chemical structures of pheromones of male Lepidoptera show a great variety, just in contrast to those of female moths 1) . Hepialus hecta L. is a species of the primitive family of Hepialidae where the males attract females after 2) sunset . For this purpose males display big hindleg scale-brushes containing volatile compounds, the smell of which has been described as wild strawberries or pineapple.

Studies on the identification and synthesis of insect pheromone: XVI. Synthesis of the optically active sex pheromone of gypsy moth and its three other optical isomers

The title compounds 1a～d were synthesized from(+)-(R)-glyceraldehyde acetonide (2) obtained from mannitol in 9～10 steps in an overall yield of 20～30%. Thus, Grignard reaction of 2 with n-C_(10)H_(21)MgBr yielded a mixture of two diastereoisomers which afforded 3(erythro form, R, S) and 4 (threo form, R, R) by SiO_2 gel chromatography. The free alcohol 3 was reacted with benzyl chloride followed by acidic hydrolysis to give diol 6 which on selective tosylation followed by treatment with 0.25 M methanolic KOH gave an epoxide 8. 8 was treated with(i-hex)_2 OuLi in ether to give 9 which on removal of the benzyl protecting group followed by reaction with HBr-HOAc gave a mixture of 11a and 11b. Finally, treatment of the mixture of 11a and 11b with 0.5M methanolic KOH gave (+)-disparlure(1a). 1c and 1d were obtained from 9 by the reaction sequences as shown in the Chinese Text. The (-)-disparlure (1b) was obtained from 4 by the reaction sequences of 5'→6'→7'→8'→9'→1b.

Iowa European corn borer sex pheromone isolation and identification of four C14 esters

Four C14 straight-chain acetate esters—(Z)-11-tetradecenyl acetate, (E)-11-tetradecenyl acetate, (E)-9-tetradecenyl acetate, and tetradecyl acetate—were isolated and identified from the diethyl ether extracts of the abdominal tips of adult female European corn borers,Ostrinia nubilalis (Hubner). The compounds were isolated using a combination of high-resolution gel-permeation, adsorption highpressure liquid, and micropreparative gas chromatography. Identifications were made by gas chromatography, a combination of gas chromatography and mass spectrometry, and microdegradative chemical methods.

Microchemical methods for the identification of volatile pheromones

Microchemical methods for the identification of volatile pheromones

Structure elucidation of insect pheromones by microanalytical methods

The isolation and identification of pheromones at the microgram level requires specialized techniques. The pheromones are obtained in the purity required for structural studies by high-speed, high-pressure liquid chromatography using silicic acid- and silver nitrate-treated columns and micropreparative GLC. Then, microchemical reactions, including hydrogenation, ozonolysis, and epoxidation are combined with infrared, nuclear magnetic resonance, and mass spectral studies to elucidate the structure of these compounds. In many cases these techniques are synergistic when combined. Thus, samples of 5–10 μg of most organic compounds under molecular weight 350 are sufficient for complete structural elucidation by using microchemical and spectroscopic techniques. The reduction in sample (2 μg) size necessary for good PMR spectra is significant because the information provided by this technique is often critical to the elucidation of a structure, and sensitivity of PMR has been one of the limiting factors in microspectroscopic analysis.

Bioassay of a Drosophila pheromone influencing sexual selection.

PHEROMONES function by transmitting information from a sending to a receiving organism by chemical means. In a classic paper, Bossert and Wilson classified the effects of such information transfer into releasing and priming1. Releaser pheromones evoke an immediate overt behavioural effect, whereas primer pheromones activate the chemoreceptor in such a way as to alter the physiology of the receiving organism1,2. In general, studies involving the isolation identification of pheromones have concentrated on releasers such as sex attractants, alarm pheromones, trail pheromones and aggregation pheromones3. The advantage of using releaser pheromones in such studies is that the behavioural effects can be observed even in a single individual of the appropriate age, sex and species. This makes the development of a relatively simple and rapid bioassay a straightforward process. So far the important exception to the use of releaser pheromones has been the work of Butler et al. showing that 9-ketodecenoic acid inhibits ovarian development in worker bees4. This substance, however, was first identified as the sex attractant of the queen bee and later shown to have a primer effect. We describe here a bioassay for a substance with an effect which does not fit easily into either the releaser or primer category.

Insect sex attractants. 13. Isolation, identification, and synthesis of sex pheromones of the male Mediterranean fruit fly.

Insect sex attractants. 13. Isolation, identification, and synthesis of sex pheromones of the male Mediterranean fruit fly.

Methodology for Isolation and Identification of Insect Pheromones with Reference to Studies on California Five-Spined Ips1

The general methodology involved in isolating and identifying insect pheromones is discussed. Examples are taken from studies of the sex attractant produced by males of the California five-spined ips, lps confusus (LeConte) Three terpene alcohols that are believed to be the principal components of the attractant were isolated and identified. These compounds are (-)-2-methyl-6-methylene-7-octen-4.01 (I), (+)-cis-verbenol (II), and (+)-2-methy 1-6-methylene-2,7-ocladien-4-o I.